Kahala Vacation Rentals

Kahala is an upscale Honolulu neighborhood that offers the best of both worlds - pristine white-sand beaches combined with the comfort of luxurious vacation rentals and all the amenities they come with. Choosing Kahala for your vacation destination comes with lots of benefits - you will be away from the hustle and bustle of Waikiki and in the same time be just a 10-minute drive away from it and its endless entertainment choices. Kahala is also within easy reach of a variety of beaches, as well as a world-class golf course. Browse through this fine selection of Kahala vacation homes below and find your perfect home away from home.

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  • Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach

    Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite ...
    Registration Number: 350020180000, GE-047-203-9424-01, TA-047-203-9424-01

    • 4 bedroom
    • 6 bathroom
    • Sleeps 9
    Hawaii> Honolulu
    18  reviews
    from $835 
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  • Hale Mahalo incl 8 seat van

    UNPARALLELED VIEWS!
    Endless hypnotizing panoramic views await you from this well maintained 3 bedroom, 3 bathroom cottage style house nestled in the highly coveted hills adjacent to Waikiki Beach.
    Our home offers over 2,000 sq ft of ...
    Registration Number: GE-007-362-3552-01, TA-007-362-3552-01, 1350230020058

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    87  reviews
    from $981 
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  • Hale Lillikoi incl 8seat van

    UNPARALLELED VIEWS!
    Endless hypnotizing panoramic views await you from this well maintained 4 bedroom, 3 bathroom cottage style house nestled in the highly coveted hills adjacent to Waikiki Beach.
    Our home offers over 2,000 sq ft of ...
    Registration Number: GE-007-362-3552-01, TA-007-362-3552-01, 1350230020058

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    37  reviews
    from $1,429 
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  • Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath

    Upscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the nearest beach, Kahala Hotel, Waialae Country club. 6-minute drive to the world famous Waikiki Beach, Diamond Head hiking, Rainbow's ...
    Registration Number: 230360390448, TA-008-444-7232-01, GE-008-444-7232-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    148  reviews
    from $1,213 
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  • Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise

    Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, ...
    Registration Number: GE-107-728-0768-01, TA-107-728-0768-01, 330310160000

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    23  reviews
    from $232 
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  • Kahala Cottage: Family fun Cottage w/Private Pool,A/C, walk to Beach and shops!

    This home-away-from-home exudes island style and comfort! Open, airy Kahala Cottage features two charming living spaces, a nicely-appointed kitchen, and a dedicated dining area that allow guests to enjoy quality time together at home. Flexible ...
    Registration Number: TA-038-170-4192-01, GE-038-170-4192-01, 350150260000

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    6  reviews
    from $340 
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  • 10% FALL SPECIAL Exclusive & Private Gated Estate, Large Family Oasis Hideaway


    Elegant, private, tropical gated estate, with lots of room to enjoy your family.
    Kahala Luxury is a spacious 6 Bedroom, 6 1/2 Bath home located in the heart of residential Kahala and is a wonderful home to spend precious family time.
    ...
    Registration Number: 350070050000, TA-153-997-3120-01, GE-153-997-3120-01

    • 5 bedroom
    • 7 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    23  reviews
    from $954 
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  • Beachfront, Kahala Mini Resort, w/2 pools, private tennis court, gated, A/C

    For discounted rates on Main house only, please inquire. 12 Night Minimum over the Christmas/New Years Holiday Season.

    Spacious beachfront estate is situated on lush tropical grounds, nestled in between palm trees. Enter the grounds ...
    Registration Number: GE-005-323-3664-01, TA-005-323-3664-01, 350060160000

    • 7 bedroom
    • 7 bathroom
    • Sleeps 14
    Hawaii> Honolulu
    15  reviews
    from $6,530 
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  • Hale Ohana incl 8 seat van

    UNPARALLELED VIEWS!
    Endless hypnotizing panoramic views await you from this well maintained 7 bedroom, 6 bathroom cottage style house nestled in the highly coveted hills adjacent to Waikiki Beach.
    Our home offers over 5,000 sq ft of ...
    Registration Number: GE-007-362-3552-01, TA-007-362-3552-01, 1350230020058

    • 7 bedroom
    • 6 bathroom
    • Sleeps 16
    Hawaii> Honolulu
    7  reviews
    from $993 
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  • Kahala Oceanside- 6 Bed/6 1/2 bath/Sleeps 14

    Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the ...
    Registration Number: 1350030350000, GE-053-250-7136-01, TA-053-250-7136-01

    • 6 bedroom
    • 7 bathroom
    • Sleeps 15
    Hawaii> Honolulu
    16  reviews
    from $4,190 
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  • It's paradise! Come & experience the calmness & serenity with the birds singing!

    STUNNING new home with views of Diamond Head, the ocean and Waikiki. Super spacious of 1980 sq. ft., immaculate 3 bedrooms (4 BEDS! King bed & 3 queen beds) and 2 full bathrooms, open floor plan, huge and well equipped kitchen with cookware, ...
    Registration Number: TA-048-102-1952-01, GE-048-102-1952-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Honolulu
    1  reviews
    from $253 
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  • Charming Historical Home - Crutchfield Estate

    This spectacular French Tudor exudes a casual elegance and the comfort of the islands. Inside you will find gleaming wood floors, an elegant fireplace, crown molding and spacious bright rooms. The kitchen is fully equipped with a new ...
    Registration Number: TA-112-501-9648-01, GE-112-501-9648-01

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    2  reviews
    from $1,602 
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  • 10% Off Summer Special! Luxury Oceanfront Estate: Banyan House

    Prices start at $150,000/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

    Banyan House is Oahu’s most luxurious vacation rental near the foot of Diamond Head. The exquisite home features...
    Registration Number: TA-199-064-7808-01, GE-199-064-7808-01, 350020500000

    • 8 bedroom
    • 10 bathroom
    • Sleeps 16
    Hawaii> Honolulu
    6  reviews
    from $5,168 
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  • Ho'okipa Villa: Historic Home+guest cottage in Kahala near the Beach w/Pool & AC

    Kahala Luxury Living

    Welcome to Ho'okipa Villa! Built in 1938 and recently renovated, this luxury home offers a unique combination of vintage and modern beach charm. Four bedrooms and three bathrooms comprise the main home, including the...
    Registration Number: TA-088-184-4224-01, 350100100000, GE-088-184-4224-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    5  reviews
    from $652 
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  • Kahala Breeze: Modern Tropical Home w/Pool, Private Yard, & A/C. Kahala Breeze

    Experience the laidback luxury and authentic island living of Kahala Breeze, a spacious four-bedroom home that features elegant decor and design cohesive with the natural beauty that surrounds it. 

    An abundance of windows in the living ...
    Registration Number: 350030310000, TA-065-534-9760-01, GE-065-534-9760-01

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    4  reviews
    from $695 
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  • Cottage with Private Salt Water Pool

    30 night minimum
    This beautiful recently updated cottage is nestled in the quiet, safe, and upscale neighborhood of Kahala. Excellent location! Just minutes to Waikiki, nearby parks and the pretty white-sand beaches of the East Honolulu ...
    Registration Number: TA-108-852-8384-01, GE-108-852-8384-01, 13526023

    • 0 bedroom
    • 1 bathroom
    • Sleeps 5
    Hawaii> Honolulu
    4  reviews
    from $218 
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  • Charming Studio Near Kahala Beach

    The perfect studio for a couple on their Hawaiian get-away who want to live like locals during their stay. Please inquire about your specific dates and we can try to accommodate your stay. This beautiful and spacious studio with 1 bathroom is ...
    Registration Number: TA-094-014-7712-01, GE-151-279-8208-01, 1350300320000

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Honolulu
    38  reviews
    from $372 
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  • Kahala Seaside: Beautiful Nautical-Themed Home w/AC, Yard, Private Pool & Spa!

    Welcome to Kahala Seaside, a spacious two-story garden view home featuring four bedrooms, three-and-a-half bathrooms, and lush garden views. Nestled in the upscale seaside burg of Kahala, you’ll have access to all the fun and excitement of ...
    Registration Number: 350040510000, TA-188-470-4768-01, GE-188-470-4768-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 7
    Hawaii> Honolulu
    1  reviews
    from $675 
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  • Luxury Resort Style Living at it's Best!

    Our Kahala Beach Apartment sits on one of the most valuable strips of beachfront in Hawaii. This Elegant apartment is Beachfront resort-style Living at its best. The Apartment is steps away from the 4 star Kahala Hotel with its Elegant dining ...
    Registration Number: GE-143-627-7248-01, TA-143-627-7248-01, 350230020174

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    2  reviews
    from $778 
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  • Hale Moana~Beachfront

    * For less than 30 day stays, please send a email onlineweb- OceanViewOahu

    At the Kahala Beach Apartments, savor the best of island life by lounging at the immaculate white sandy beach, take a plunge in the complex's luxurious ocean-front...
    Registration Number: GE-007-362-3552-01, TA-007-362-3552-01, 1350230020058

    • 3 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    1  reviews
    from $742 
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